Sodium Hydroxide → (2,6-Dichloropyridin-4-yl)-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,6-d]selenophen-4-ylamine

HRID 1529817Notes

Reaction equation

HRID 1529817 reaction equation
Cl[C:2]1[C:7]2[C:8]3[CH2:14][CH2:13][CH2:12][CH2:11][C:9]=3[Se:10][C:6]=2[N:5]=[CH:4][N:3]=1.[NH2:15][C:16]1[CH:21]=[C:20]([Cl:22])[N:19]=[C:18]([Cl:23])[CH:17]=1.[OH-].[Na+]>CN(C=O)C>[Cl:23][C:18]1[CH:17]=[C:16]([NH:15][C:2]2[C:7]3[C:8]4[CH2:14][CH2:13][CH2:12][CH2:11][C:9]=4[Se:10][C:6]=3[N:5]=[CH:4][N:3]=2)[CH:21]=[C:20]([Cl:22])[N:19]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 1376524-Amino-2,6-dichloropyridineHCID 867005014-Chloro-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,4-d]selenophene

Product 1

HCID 57377307(2,6-Dichloropyridin-4-yl)-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,6-d]selenophen-4-ylamineYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-chloro-5,6,7,8-tetrahydrobenzo[1,2-b]pyrimidino[5,4-d]selenophene (470 mg, 1.72 mmol, from step b of example 1) in DMF (10 mL) was added sequentially 4-amino-2,6-dichloropyridine (420 mg, 2.58 mmol) and powdered NaOH (210 mg, 5.16 mmol) at rt and the mixture was stirred at rt for 16 h. Work-up of the mixture as described in example 2, gave the product as a pale yellow color solid (500 mg, 73%), mp 238-242° C. 1H NMR (400 MHz, DMSO-d6): δ 9.00 (1H, s, exchangeable with D2O), 8.62 (1H, s), 7.76 (2H, s), 3.07 (2H, br s), 2.94 (2H, br s), 1.84 (4H, br s); 13C NMR (100 MHz, DMSO-d6): δ 172.3, 153.1, 151.3, 151.0, 149.2, 140.5, 128.3, 122.3, 112.1, 27.7, 26.7, 22.6, 21.9; LC-MS (negative ion mode): m/z 395, 397, 399 (M−H)−.

Sources & evidence

ORD record
ord-fb0ef39d976f4c36884a5a93c98b8bc4
Source dataset
uspto-grants-2015_07
Patent number
US09090633B2

Reaction notes

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